CA1310537C - Hydantoins as animal food supplements - Google Patents
Hydantoins as animal food supplementsInfo
- Publication number
- CA1310537C CA1310537C CA000547566A CA547566A CA1310537C CA 1310537 C CA1310537 C CA 1310537C CA 000547566 A CA000547566 A CA 000547566A CA 547566 A CA547566 A CA 547566A CA 1310537 C CA1310537 C CA 1310537C
- Authority
- CA
- Canada
- Prior art keywords
- hydantoin
- protein
- analogue
- dry weight
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001469 hydantoins Chemical class 0.000 title claims abstract description 55
- 241001465754 Metazoa Species 0.000 title claims abstract description 22
- 235000015872 dietary supplement Nutrition 0.000 title description 4
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 45
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 45
- 235000013305 food Nutrition 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 19
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 14
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 13
- 229940091173 hydantoin Drugs 0.000 claims description 13
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000004474 valine Substances 0.000 claims description 8
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 7
- 229960000310 isoleucine Drugs 0.000 claims description 7
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 159000000007 calcium salts Chemical class 0.000 claims description 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 235000005974 protein supplement Nutrition 0.000 claims description 3
- 229940116540 protein supplement Drugs 0.000 claims description 3
- GHKHZJHMIBYCPG-UHFFFAOYSA-N 5-propan-2-ylideneimidazolidine-2,4-dione Chemical compound CC(C)=C1NC(=O)NC1=O GHKHZJHMIBYCPG-UHFFFAOYSA-N 0.000 claims 4
- ZCXMFCJBFWJWBA-UHFFFAOYSA-N 5-butan-2-yl-5-hydroxyimidazolidine-2,4-dione Chemical compound CCC(C)C1(O)NC(=O)NC1=O ZCXMFCJBFWJWBA-UHFFFAOYSA-N 0.000 claims 1
- 235000020776 essential amino acid Nutrition 0.000 abstract description 15
- 239000003797 essential amino acid Substances 0.000 abstract description 15
- 235000018102 proteins Nutrition 0.000 description 25
- 229940024606 amino acid Drugs 0.000 description 17
- 235000001014 amino acid Nutrition 0.000 description 17
- 150000001413 amino acids Chemical class 0.000 description 16
- 229960003136 leucine Drugs 0.000 description 10
- BKAJNAXTPSGJCU-UHFFFAOYSA-N 4-methyl-2-oxopentanoic acid Chemical compound CC(C)CC(=O)C(O)=O BKAJNAXTPSGJCU-UHFFFAOYSA-N 0.000 description 9
- 235000005911 diet Nutrition 0.000 description 8
- 230000037213 diet Effects 0.000 description 8
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 8
- 239000013589 supplement Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 235000006109 methionine Nutrition 0.000 description 7
- 229930182817 methionine Natural products 0.000 description 7
- 239000004470 DL Methionine Substances 0.000 description 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 150000004715 keto acids Chemical class 0.000 description 6
- 235000016709 nutrition Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 125000000468 ketone group Chemical group 0.000 description 5
- 235000013336 milk Nutrition 0.000 description 5
- 210000004080 milk Anatomy 0.000 description 5
- 239000008267 milk Substances 0.000 description 5
- 230000000050 nutritive effect Effects 0.000 description 5
- 229960004295 valine Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 230000002503 metabolic effect Effects 0.000 description 4
- 235000019645 odor Nutrition 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 3
- 241000282849 Ruminantia Species 0.000 description 3
- 235000019728 animal nutrition Nutrition 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- -1 isoProPyl Chemical group 0.000 description 3
- 208000017169 kidney disease Diseases 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 229960004452 methionine Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 210000004767 rumen Anatomy 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100036238 Dihydropyrimidinase Human genes 0.000 description 2
- 208000035240 Disease Resistance Diseases 0.000 description 2
- 206010013911 Dysgeusia Diseases 0.000 description 2
- 102000002322 Egg Proteins Human genes 0.000 description 2
- 108010000912 Egg Proteins Proteins 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 2
- 229930195722 L-methionine Natural products 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 108091022884 dihydropyrimidinase Proteins 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
- 210000002969 egg yolk Anatomy 0.000 description 2
- 239000006052 feed supplement Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- LTJNSPQCECGDTR-BYOYUIHVSA-N (2S)-2-amino-4-methylpentanoic acid 5-butan-2-yl-5-hydroxyimidazolidine-2,4-dione 5-(2-methylpropylidene)imidazolidine-2,4-dione Chemical compound CC(C)C[C@H](N)C(O)=O.CC(C)C=C1NC(=O)NC1=O.CCC(C)C1(O)NC(=O)NC1=O LTJNSPQCECGDTR-BYOYUIHVSA-N 0.000 description 1
- NORRZDQNYVIRJK-VWMHFEHESA-N CC(C)[C@H](N)C(O)=O.CC(C)=C1NC(=O)NC1=O Chemical compound CC(C)[C@H](N)C(O)=O.CC(C)=C1NC(=O)NC1=O NORRZDQNYVIRJK-VWMHFEHESA-N 0.000 description 1
- GJQOEKFZYOPNBK-BFEIYTHUSA-N CC[C@H](C)[C@H](N)C(O)=O.CCC(C)=C1NC(=O)NC1=O.CC(C)C1(O)NC(=O)NC1=O Chemical compound CC[C@H](C)[C@H](N)C(O)=O.CCC(C)=C1NC(=O)NC1=O.CC(C)C1(O)NC(=O)NC1=O GJQOEKFZYOPNBK-BFEIYTHUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000122871 Caryocar villosum Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 125000002066 L-histidyl group Chemical class [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 108010064851 Plant Proteins Proteins 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000010399 Wasting Syndrome Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 235000021245 dietary protein Nutrition 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/807—Poultry or ruminant feed
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fodder In General (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/911,688 US4744990A (en) | 1986-09-25 | 1986-09-25 | Hydantoins as animal food supplements |
| US911,688 | 1986-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1310537C true CA1310537C (en) | 1992-11-24 |
Family
ID=25430696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000547566A Expired - Lifetime CA1310537C (en) | 1986-09-25 | 1987-09-23 | Hydantoins as animal food supplements |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4744990A (de) |
| EP (1) | EP0261982A1 (de) |
| JP (1) | JP2644500B2 (de) |
| AU (1) | AU7865387A (de) |
| CA (1) | CA1310537C (de) |
| NZ (1) | NZ221548A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871552A (en) * | 1986-09-25 | 1989-10-03 | W. R. Grace & Co.-Conn. | Hydantoins as animal food supplements |
| SE462463B (sv) * | 1988-12-02 | 1990-07-02 | Decken Alexandra V D | Livs- och fodermedel innehaallande ketosyror |
| DE19529211C2 (de) * | 1995-08-09 | 1999-01-14 | Degussa | Verfahren zur Herstellung von (R)-tertiär-Leucin |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA669828A (en) * | 1963-09-03 | Tchelitcheff Serge | Animal feeding stuffs | |
| DE1965921A1 (de) * | 1968-11-20 | 1971-08-12 | Hoechst Ag | Verwendung von Thiohydantoinen als Zusatz zu Mastfutter fuer Tiere,insbesondere Rinder |
| DE1965922A1 (de) * | 1968-11-20 | 1971-06-24 | Hoechst Ag | Neue chemische Verbindungen und Verfahren zu ihrer Herstellung |
| US3644629A (en) * | 1969-01-21 | 1972-02-22 | Du Pont | Method for improving animal feed efficiency and compositions suitable for use therein |
| AT317662B (de) * | 1971-05-15 | 1974-09-10 | Farmaceutici Italia | Tierwachstumfördernde Futtermittel |
| IT987278B (it) * | 1973-05-11 | 1975-02-20 | Snam Progetti | Procedimento per la preparazione di l carbamil ammino acidi e dei corrispondenti l amminoacidi |
| FR2229355B1 (de) * | 1973-05-17 | 1977-10-21 | Anic Spa | |
| US4100293A (en) * | 1974-04-15 | 1978-07-11 | The Johns Hopkins University | Treatment of hepatic disorders with therapeutic compositions comprising keto analogs of essential amino acids |
| US4065571A (en) * | 1974-06-11 | 1977-12-27 | Canada Packers Limited | Antiviral 5-(substituted benzal) hydantoins |
| US4175198A (en) * | 1976-10-07 | 1979-11-20 | W. R. Grace & Co. | 5-Secondary alkylidene hydantoins |
| US4101679A (en) * | 1977-05-31 | 1978-07-18 | Chevron Research Company | Cellulose fermentation process |
| US4228099A (en) * | 1978-03-17 | 1980-10-14 | The Johns Hopkins University | Ornithine and arginine salts of branched chain keto acids and uses in treatment of hepatic and renal disorders |
| US4320146A (en) * | 1978-03-17 | 1982-03-16 | The Johns Hopkins University | Treatment of hepatic and renal disorders with ornithine and arginine salts of branched chain keto acids |
| US4352814A (en) * | 1979-04-18 | 1982-10-05 | The Johns Hopkins University | Treatment of hepatic and renal disorders with mixed salts of essential or semi-essential amino acids and nitrogen-free analogs |
| US4296127A (en) * | 1979-04-18 | 1981-10-20 | The Johns Hopkins University | Mixed salts of essential or semi-essential amino acids and nitrogen-free analogs thereof |
-
1986
- 1986-09-25 US US06/911,688 patent/US4744990A/en not_active Expired - Lifetime
-
1987
- 1987-08-24 NZ NZ221548A patent/NZ221548A/xx unknown
- 1987-09-18 AU AU78653/87A patent/AU7865387A/en not_active Abandoned
- 1987-09-21 JP JP62235064A patent/JP2644500B2/ja not_active Expired - Lifetime
- 1987-09-23 CA CA000547566A patent/CA1310537C/en not_active Expired - Lifetime
- 1987-09-25 EP EP87308509A patent/EP0261982A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0261982A1 (de) | 1988-03-30 |
| US4744990A (en) | 1988-05-17 |
| JPS6398356A (ja) | 1988-04-28 |
| AU7865387A (en) | 1988-03-31 |
| JP2644500B2 (ja) | 1997-08-25 |
| NZ221548A (en) | 1990-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |